4-amino-6-(2,4-dichlorophenyl)-2-(methylthio)pyrimidine-5-carbonitrile | 737765-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-amino-6-(2,4-dichlorophenyl)-2-(methylthio)pyrimidine-5-carbonitrile
• 英文别名: 4-Amino-5-cyano-2-methylthio-6-(2,4-dichlorophenyl)-pyrimidine；4-amino-6-(2,4-dichlorophenyl)-2-methylsulfanylpyrimidine-5-carbonitrile
• CAS: 737765-03-6
• 化学式: C₁₂H₈Cl₂N₄S
• 分子量: 311.194
• InChiKey: GECCQKWTZDYJML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-6-(2,4-dichlorophenyl)-2-(methylthio)pyrimidine-5-carbonitrile 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-Aminomethyl-6-(2,4-dichloro-phenyl)-2-morpholin-4-yl-pyrimidin-4-ylamine
  参考文献：
  名称：

  An aminomethylpyrimidine DPP-IV inhibitor with improved properties

  摘要：

  A recently identified DPP-IV inhibitor (1) was found to induce phospholipidosis and to inhibit CYP3A4. A small series of less lipophilic and less amphiphilic analogues was synthesized in an effort to overcome these issues. One compound from this series was equipotent to 1, did not induce phospholipidosis and showed a reduced CYP3A4 inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.048
• 作为产物：
  描述：

  2-[(2,4-二氯苯基)亚甲基]丙二腈 、 S-甲基异硫脲硫酸盐 在 potassium carbonate 、 potassium permanganate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.5h， 以88%的产率得到4-amino-6-(2,4-dichlorophenyl)-2-(methylthio)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  An aminomethylpyrimidine DPP-IV inhibitor with improved properties

  摘要：

  A recently identified DPP-IV inhibitor (1) was found to induce phospholipidosis and to inhibit CYP3A4. A small series of less lipophilic and less amphiphilic analogues was synthesized in an effort to overcome these issues. One compound from this series was equipotent to 1, did not induce phospholipidosis and showed a reduced CYP3A4 inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.048

文献信息

• An Environmentally Benign Multicomponent Synthesis of Some Novel 2-Methylthio Pyrimidine Derivatives Using MCM-41-NH₂as Nanoreactor and Nanocatalyst
  作者：Shahnaz Rostamizadeh、Masoomeh Nojavan

  DOI：10.1002/jhet.1755

  日期：2014.3

  Some novel 4‐amino‐6‐aryl‐2‐methylthio pyrimidine‐5‐carbonitrile derivatives were synthesized through a one‐pot three‐component reaction of an aldehyde, malononitrile, and S‐methylisothiouronium iodide, using MCM‐41‐NH2 as nanoreactor and nanocatalyst. This protocol has some advantages including application of readily available and nonhazardous materials, benign reaction conditions (ambient temperature

  一些新的4-氨基-6-芳基-2-甲硫基嘧啶-5-甲腈衍生物是通过醛，丙二腈的一锅三组分反应合成，并且小号-methylisothiouronium碘化物，使用MCM-41-NH 2如纳米反应器和纳米催化剂。该方案具有一些优点，包括应用容易获得且无害的材料，良性反应条件（环境温度，无溶剂和一锅法），易于加工且产品的总收率高。
• Synthesis of N2-arylaminopyrimidine-5-carbonitrile derivatives via SNAr amination reaction
  作者：Shahnaz Rostamizadeh、Masoomeh Nojavan、Reza Aryan

  DOI：10.1016/j.cclet.2014.10.007

  日期：2015.1

  An efficient and high-yielding synthesis of N-2-arylaminopyrimidine-5-carbonitrile derivatives starting from arylamines and 2-methylthio-pyrimidine-5-carbonitrile derivatives has been developed in the presence of cesium carbonate as basic reagent. This new protocol showed high chemical tolerance for a range of functional groups, and only the methylthio substituent on C2 of the pyrimidine ring was replaced with arylamine derivatives under the reaction conditions. (C) 2014 Shahnaz Rostamizadeh. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.